(Z)-5-[2-(Benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole methanol monosolvate, C19H16N4O2S·CH3OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,5-dimethoxyphenyl)acrylonitrile with tributyltin azide via a [3 + 2]cycloaddition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole, C20H18N4O3S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thiophen-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile with tributyltin azide. Crystals of (I) have two molecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzothiophene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetrazole rings of (I) and (II) make dihedral angles with the mean planes of the benzothiophene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The dimethoxyphenyl and trimethoxyphenyl rings make dihedral angles with the benzothiophene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, molecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetrazole and methanol, and are parallel to the b axis. In (II), molecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetrazole rings.
Digital Object Identifier (DOI)
The authors gratefully acknowledge the Arkansas Research Alliance for financial support, the UAMS sub award to PNR and SA from NIA Claude Pepper Center grant P30-AG028718 (J. Wei, P.I.) and the NIH/National Institute of General Medical Sciences (P20GM109005) for a COBRE award.
Supporting information: this article has supporting information at journals.iucr.org/d.
Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989016005600/hg5472sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S2056989016005600/hg5472Isup2.hkl
Structure factors: contains datablock II. DOI: 10.1107/S2056989016005600/hg5472IIsup3.hkl
3D view of crystallographic information
Penthala, Narsimha Reddy; Yadlapalli, Jaishankar K. B.; Parkin, Sean; and Crooks, Peter A., "Crystal Structures of (Z)-5-[2-(benzo[b]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1H-tetrazole and (Z)-5-[2-(benzo[b]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1H-tetrazole" (2016). Chemistry Faculty Publications. 80.